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【结 构 式】

【分子编号】34986

【品名】methyl (5R,6S,7S)-7-([[tert-butyl(dimethyl)silyl]oxy]methyl)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate

【CA登记号】

【 分 子 式 】C29H38O9Si

【 分 子 量 】558.70082

【元素组成】C 62.34% H 6.86% O 25.77% Si 5.03%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXXII)

The oxidation of (XXXI) with pyridinium dichromate (PDC) gives the ketoester (XXXII). The reaction of (XXXII) with formaldehyde/NaOH and then with p-toluenesulfonic acid gives the hydroxymethyl lactone (XXXIII), which is submitted to a thermal extrusion of formaldehyde yielding (XXXIV). The regioselective reduction of the ketonic group of (XXXIV) with LiAl(OtBU)3H in THF affords hydroxylactone (XXXV) with undesired steric configuration at the lactone ring. The silylation of (XXXV) with TBDMS-OTf affords the silyl ether (XXXVI), which is isomerized with LiHMDS in THF giving (XXXVII) with the right configuration. Finally, this compound is desilylated to the target compound with triethylammonium fluoride in acetonitrile.

1 Andrews, R.C.; et al.; Asymetric total synthesis of (-)-podophyllotoxin. J Am Chem Soc 1988, 110, 23, 7854.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXI) 34985 methyl (5R,6S,7S)-7-([[tert-butyl(dimethyl)silyl]oxy]methyl)-8-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate C29H40O9Si 详情 详情
(XXXII) 34986 methyl (5R,6S,7S)-7-([[tert-butyl(dimethyl)silyl]oxy]methyl)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate C29H38O9Si 详情 详情
(XXXIII) 34987 (5aS,8aS,9R)-5a-(hydroxymethyl)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione C23H22O9 详情 详情
(XXXIV) 34988 (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione C22H20O8 详情 详情
(XXXV) 34989 (5R,5aS,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one C22H22O8 详情 详情
(XXXVI) 34990 (5R,5aS,8aR,9R)-9-[[tert-butyl(dimethyl)silyl]oxy]-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one C28H36O8Si 详情 详情
(XXXVII) 34991 (5R,5aR,8aR,9R)-9-[[tert-butyl(dimethyl)silyl]oxy]-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one C28H36O8Si 详情 详情
Extended Information